A few years ago I dated a rich lady. I had no idea she was rich when we first met for a movie, courtesy of Craigslist. She walked up shyly along 23rd Street, dressed like an office worker, not short but not tall. Cute as hell.

“Steve?” she said.

"No, sorry," I said with a blank expression.

She laughed, falling forward a little, and followed me toward the box office.

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We sat on a couch in the theater lobby before showtime and she showed me her knees. They’d gotten scratched up as she tripped over a curb in the rush to make it here on time after work. I was too happy that she’d turned out adorable to remember any chivalry, like seeing if management had any Band-Aids in the back office. But she wasn’t bleeding anyway, just a little scuffed, and she was laughing it off. The chemistry was crazy good. Right off, we could make each other smile and laugh with ease. We were both writers, and both introverts, though of different varieties. She was the kind who didn’t suffer fools lightly; I was, and still am, the kind who indulges fools endlessly. At any rate, she was my kind of weird.

We watched a movie called Eastern Promises, in which various non-Russian actors pretended to be Russian gangsters. It was grisly fun. Afterward, we sat on another couch to tell capsule versions of our life stories. That’s when I learned that she was no office worker, but an executive who made in a year more than my entire gross income for the previous decade. She had arrived in the U.S. a poor immigrant child and followed in her mother’s footsteps, which took her from welfare and squalor to running a successful business. She grew up to become a journalist, and a poet, and then an executive in a major public relations firm.

Suddenly I was torn. I hated rich folks. Even their kindest, most sincere gestures carried an undertone of arrogance and entitlement. Even self-made, liberal, all-embracing rich people. So now my prejudice took the softness out of her pretty face, the warmth out of her dazzling smile. She was one of them. No wonder she was so laid back. The world is their living room, after all.

Later she shot me a sarcastic email, teasing me for “interrogating me about my finances” that night.

We ended up going out to the movies and exploring the city most weekends for the following year and a half. Early on, she warned me that she was recovering from a terrible breakup and that, because I reminded her of her ex, another poor young creative type, it was best that she didn’t exploit this resemblance sexually just to assuage loneliness, since "you have already become way too important to me to lose.” Shit. Exploit me, baby. I ain’t that important.

But that door remained locked, even as we grew so close that she would say the most romantic-sounding things to me: “Even your nonsense makes sense to me,” and “I haven’t been happy for a very long time, but I’m happy whenever I’m with you.”

That year we had little adventures all over the city. Coney Island, Fort Tryon Park, Harlem, Prospect Park, the Lower East Side; museums, parades, markets, performance spaces, comedy clubs, noodle restaurants. And nearly every arthouse movie theater in NYC. I'd roamed this city pretty widely on my own over the years, but never so much with any one companion. She had a genius for digging up new haunts and people-watching perches. I jokingly called her my one-woman Fresh Air Fund. Even apart, we traded thousands of laughs, heady, goofy, loving talks and emails, elaborate conspiracies of silliness.

Since she lived simply, dressing in her frugal Berkeley bohemian style and indulging only one great vice, books, our class mismatch wasn't too apparent. Only four months into our thing, I'd lost my job as a security guard and went homeless. I didn't share the grisly details with her because, despite our clearcut status as pals, I was unconsciously campaigning for a promotion.

By that time I was working for a webcasting company but living in one of the illegal boarding houses to which the city referred some of its homeless cases, deep in East New York, Brooklyn. It was basically a box-shaped apartment house identical to the ones to the left and right of it, except that inside, the rooms on each of its three floors contained two to three bunk beds accomodating four to six men. Nearly 40 men in one house. On my floor, a two-bedroom apartment housed 12 of us. My bunk was in what would normally have been the living room. I slept beside the open kitchen, my head near the freezer door. The 3 train roared all night over our heads, along the elevated tracks on Livonia Avenue. On broiling summer nights, there were concerts of gunshots. You got used to it.

On weekends, I would meet the lady for our outings. Sometimes we'd just find a coffee house where we could sit and write together, looking up occasionally from notebook or laptop to exchange jokes and ideas. She called it our Productivity Club.

Other times we'd end up doing the kinds of things I supposed real couples got into, like our dreamlike day at Jones Beach, where the surf tossed her into my arms and I realized I was in love with her. That night back in East New York, climbing into my high bunk in the dark, I set down my sand-caked shoes and whispered, "Damn."

The following week, when I pressed the issue and got the answer I didn't want to hear, I requested a separation to clear my head. She honored the request, reluctantly, sadly. I was messing up a good thing we had going.

We resumed our friendship after a couple of months, when I declared myself fit and ready to be her true friend again, and somehow we ended up having sex. Well now. I assumed it was her way of killing off an ailing friendship for good. As deaths go, it was pretty spectacular.

Sitting up in her bed afterward, I found I couldn’t sleep. Here was this beautiful, brilliant woman from a world in which I could never be comfortable. Intellectuals, academics, power brokers. She had known it that first night at the movies. She knew I wasn’t the one; just another companion to help pass the time. I understood it only now, watching her sleep in the darkness, and looking around at her tiny apartment. It was the studio of a girl after my own heart, yes, full of books and quirk and plastic gorillas. But its location in the pricey crossroads of SoHo, Chinatown and Little Italy spoke of an accomplished life, rooted in steady tradition and a sense of purpose.

I didn't know much about tradition or purpose. I knew about its synthetic substitutes, consolation prizes like Black History Month and affirmative action. Where I lived and felt (relatively) comfortable,but history had encoded folks at almost the DNA level with the servile, hostile instincts of slave and colonial subject.

She woke up and rolled over to ask, “What’s wrong?” I proceeded with a long, incoherent speech about how there are some folks in this city who have nowhere to go, neither “up” nor “down.” I told her our association made no sense, even if it made perfect sense. She laughed: “My bed is where guys come to have their existential crises.”

She never needed to hear my crazy speeches to know what was wrong with me, but she always let me get it out anyway. Then she would deliver a wise prescription. In this case, it was, “You are always very clear on what you don’t like, what you don’t want to do. Now maybe figure out what you do want to do.”

I shrugged. “I…”

“You want to make films,” she said. “I know you, silly. You should get started on that right away.”

A few months later, I disappeared from her life again, not wanting to stick around to see her marry some CEO or architect. I got back into making no-budget films in exactly the amateurish, personal way I loved but had foolishly avoided since film school and the industry taught me that there’s no money in it. What the lady taught me about myself was invaluable: I don’t give a damn about money.

I realized I wanted to become something rarer than an albino alligator and guaranteed to be perceived as foolish: a working-class film artist and writer. (My best friend, the graffiti artist SnailsOne, recently reminded me that the old-school graf artists that she painted with in the '90s were all working-class joes. They never sought money for their creations but painted on their off-hours for pleasure, and to endure as true urban legends. They have a hilarious derogatory name for gallery sellouts: toys.)

But when you come from a working-class background like mine, the assumption is that, if you have any sense, you’ll do whatever it takes to climb into the middle class. You’ll get educated up to a professional standard that ensures a comfortable lifestyle. Only the spoiled children of the upper middle class and wealthy scorn money, and even then, only for a rebellious season. Certainly no black man like me, knowing how hard it is to get anywhere in this white man’s world, will turn his back to opportunities that possibly come around but once a lifetime, if ever. But I do just that, all the time.

Then again, in these times, it's possible for a fool like me to achieve, and build, and gain, even if there's not much in the way of material payoff. The internet and cheap media-creation tools that exist now make it possible for a guy at the bottom of society to reach folks on all strata, across the globe. For someone who isn't necessarily looking for a career, but to get something simple and vital said before he leaves this earth, this is a miracle. It's a blessing.

When I write on this site about poverty and homelessness in New York, as experienced by me and some people I know, it's because I think it's useful for people who aren't poor to know about it, and because hopefully it makes for a good story. It's not a solicitation for pity. My years off the grid have been the freest and happiest of my life.

But the fact is there's loneliness, too. That's just the way it is, when you've got the wrong kind of ambition in a city full of potential partners who are still chasing a beguiling 20th-century notion of the American dream.

Steven Boone is a film critic who has been writing for Capital about his experiences with homelessness. His previous installments are here.